• Title/Summary/Keyword: $catechin-7-O-\

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Nitric Oxide Production Inhibitory and Anti-Oxidative Activities of Phenolic Compounds from the Barks of Ulmus davidiana

  • Lee, Jae-Hee;Yeom, Seung-Hwan;Kim, Min-Kee;Kim, Hyun-Jung;Sim, Jae-Geul;Lee, Min-Won
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.196.2-196.2
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    • 2003
  • The Barks of Ulmus davidiana (Ulmaceae) have been used for the treatment of insecticide, anti-boil and anti-fungi in Korean traditional medicine. Four phenolic compounds were isolated from 80% Acetone extracts. The structures of these compounds were elucidated as (+)-catechin, (+)-catechin 7-O-${\beta}$-D-glucopyranoside, (+)-catechin 7-O-${\beta}$-D-xylopyranoside and procyanidin B-1. These phenolic compounds showed significant nitrogen monoxide(NO) production inhibitory activity in IFN-${\gamma}$, LPS stimulated RAW 264.7 cell and also showed significant antioxidative activity on DPPH radical. (omitted)

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Chemical Constituents of Domestic Quercus spp. Barks (국내산 참나무속 수종 수피의 추출성분)

  • Kim, Jin-Kyu;Kwon, Dong-Joo;Lim, Soon-Sung;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.38 no.4
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    • pp.359-374
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    • 2010
  • This study was carried out to investigate the chemotaxonomical correlation and chemical constituents of domestic Quercus spp. barks. The barks of Q. mongolica, Q. aliena, Q. serrata, Q. acutissima, Q. dentata, and Q. variabilis were collected in the experimental forest of Kangwon National University. The combined extracts were successively fractionated with n-hexane, methylene chloride and ethyl acetate using a separation funnel. A portion of the ethyl acetate and H2O soluble materials of each species were chromatographed on a Sephadex LH-20 column using various aqueous MeOH and EtOH-hexane as washing solvents. Spectrometric analysis such as NMR and MS, including TLC, were performed to characterize the structures of the isolated compounds. Ellagic acid (0.03 g), (+)-catechin (4.59 g), taxifolin (3.35 g), and glucodistylin (20.52 g) were isolated from Q. mongolica bark. Gallic acid (0.18 g), (+)-catechin (8.52 g), (+)-gallocatechin (0.09 g), taxifolin (0.54 g), and glucodistylin (3.28 g) were characterized from Q. acutissima bark. Gallic acid (0.38 g), ellagic acid (0.11 g), (+)-catechin (2.01 g), (+)-gallocatechin (0.12 g), and glucodistylin (0.39 g) were identified from Q. dentata bark. Ellagic acid (1.51 g), (+)-catechin (21.91 g), and glucodistylin (3.91 g) were purified from Q. aliena bark. Ellagic acid (0.84 g), (+)-catechin (0.82 g), taxifolin (4.02 g), and glucodistylin (21.50) were isolated from Q. serrata bark. Gallic acid (0.24 g), caffeic acid (0.05 g), (+)-catechin (0.32 g), and glucodistylin (0.65 g) were purified from Q. variabilis bark. (+)-Catechin and glucodistylin were isolated from all the barks. Glucodistylin can be a taxonomic index on Quercus spp.

Extractives from the Needles of Torreya (벼자나무 잎의 추출성분)

  • Kim, Jin-Kyu;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.29 no.4
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    • pp.53-59
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    • 2001
  • The needles of torreya(Torreya nucifera S. et Z) were collected, extracted with acetone-$H_2O$(7:3, v/v), fractionated with hexane, chloroform and ethylacetate, and freeze dried to give some dark brown powder. The ethylacetate soluble mixture was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents. Most of the needle extractives were flavan and its methyl ether compounds such as (+)-catechin, (-)-epicatechin, (+)-gallocatechin, (-)-epigallocatechin, 3'-O-methyl-(+)-catechin and 3'-O-methyl-(-)-epicatechin including protocatechuic acid, one of benzoic acids. $^1H$- and $^{13}C$-NMR, NOE and CI-MS analyses were performed to elucidate the structures of the isolated compounds.

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Extractives from the needles of Juniperus rigida Siebold et Zucearin and Antioxidant activity (노간주나무(Juniperus rigida Siebold et Zucearini) 잎의 추출성분 및 항산화 활성)

  • Lee, Sang-Keug;Kim, Jin-Kyu;Ham, Yeon-Ho;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.32 no.1
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    • pp.59-66
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    • 2004
  • The dried neeldes(1.5 kg) of Juniperus rigida were ground, extracted with acetone-H2O(7:3, v/v), concentrated, and fractionated with a series of hexane, CH2Cl2, EtOAc and water on a separatory funnel. Each fraction was freeze dried to give dark-brown powder and EtOAc and water soluble fractions were chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluent. Spectrometric analysis such as NMR and FAB or EI-MS including TLC were performed to characterize the structures of the isolated compounds. The needles of Juniperus rigida contained a large amount of (+)-catechin, quercetin-3-O-α-L-rhamnopyranoside and isoconiferin, in addition to a small amount of umbelliferone and quercetin-3-O-β-D-rutinoside. The antioxidative activities of each fraction and isolated compounds were tested by DPPH radical scavenging method, and EtOAc soluble fraction, (+)-catechin and quercetin-3-O-α-L-rhamnopyranoside were effective.

Studies on the Antioxidative Substances in the Seeds of the Rutaceae Family (운향과(芸香科) 식물(植物) 종실(種實)의 항성화성(抗醒化性))

  • Kim, Seong-Jin;Kim, Ji-Soo;Joh, Yong-Goe
    • Journal of the Korean Applied Science and Technology
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    • v.11 no.1
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    • pp.7-16
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    • 1994
  • Some seeds of the Rutaceae family, Zanthoxylum piperitum, Z. schinifolium officinalis, Poncirus trifoliata, Citrus unshin, were investigated to clarify their antioxidative components. Finely powdered samples were extracted by hexane, followed by dichioromethane and then 70% methanol in a hot bath. Its unsaponifiables containing X-and Y-tocopherol with trace amount of ${\beta}-and$\;{\delta}-tocopherol$. also showed comparatively weak activity, although the hexane fraction itself had no significant antioxidative effect on lard. Levels of total tocopherols in the samples averages 42. 24-154. 11 mg/lOOg total extractives. The dichloromethane-and 70% methanol extractives showed strong antioxidative activity, from which antioxidative substances were purified with benzene-acetone(6:5, V/V) on a silica gel column, and with a solvent mixture of acetonitrile-methanol-$H_2O$(40:40:20, V/V/V) on a Sep-Pak $C_{18}$ hydrolyzed by 5% KOH-ethanol. The recovered unsaponifiables were, then, separated on a column of high performance liquid chromatography. The unsaponifiables produced by hydrolysis of the isolates from dichloromethane extractives has epi-catechin(40.0-57.1%) and (+)-catechin<$l9.1{\sim}24.4%$ to total phenolic substances, on area base) as major component, accompanied by chlorogenic acid, gallic acid(?), trans-p-coumaric acid and tralls-p-ferulic acid including some unknown components, and those derived from 70% methanol extractives also comprise (+)-catechin($31.3{\sim}39.6%$ to total components, on area base), epi-catechin($2O.2{\sim}36.4%$), trans-p-cournaric acid(8.4-15.3%) and trans-p-ferulic acid($7.7{\sim}14.1%$) as predominant component with some minor coponents, but the fraction supposed to be gallic acid(?) is not present. The antioxidative activities of the phenolic components isolated in this work were in order of epi-catechin>catechin>chlorogenic acid>trans-p-ferluic acid>trans-p-coumaric acid.

Phenolic Compounds on the Leaves of Betula Platyphylla var. latifolia

  • Lee, Min-Won;Takashi Tanaka;Gen-Ichiro Nonaka;Hahn, Dug-Ryoung
    • Archives of Pharmacal Research
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    • v.15 no.3
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    • pp.211-214
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    • 1992
  • Chemical examination of Betula platyphylla var. latifolia afforded a novel diarylheptanoid named betulateraol, together with a phenylpropanoid (3, 4'-dihydroxypropio-phenone), flavan-3-ol [(+)-catechin] and its glycosides [(+)-catechin 5-O-$\beta$-glucopyranoside, (+)-catechin 7-0-$\beta$-D-glucopyranoside] and two proanthocyanidins (procyanidins B-1 and B-3).

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Chemical Constituents of Domestic Quercus spp. Leaves (국내산 참나무속 수종 잎의 추출성분)

  • Kim, Jin-Kyu;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.34 no.6
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    • pp.61-71
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    • 2006
  • This study was carried out to investigate chemotaxonomical correlation an d the chemical constituents of domestic Quercus sp. leaves. The leaves of Q. mongolica, Q. aliena, Q. serrata, Q. acutissima, Q. dentata and Q. variabilis were collected in the experimental forest of Kangwon National University. The combined extracts were successively fractionated with n -hexane, methylene chloride and ethyl acetate using a separation funnel. A portion of the ethyl acetate and $H_2O$ soluble materials of each species were chromatographed on a Sephadex LH-20 column using various aqueous MeOH and EtOH-hexane as washing solvents. Spectrometric analysis such as NMR and MS, including TLC, were performed to characterize the structures of the isolated compounds. Gallic acid, (+)-catechin, (-)-epicatechin, (+)-gallocatechin, kaempferol, astragalin, astragalin-6"-O-gallate, isoquercitrin, isoquercitrin-6"-O-gallate and myricetin were isolated from Q. mongolic a leaves. Gallic acid, kaempferol and quercetin were characterized from Q. acutissima leaves. Gallic acid, (+)-catechin, (-)-epicatechin, (+)-gallocatechin, (-)-epigallocatechin, kaempferol, quercetin, guajaverin and tamarixin were identified from Q. dentata leaves. Gallic acid, (+)-catechin, (-)-epicatechin, kaempferol, quercitrin, isoquercitrin and myricetin were purified from Q. serrata leaves. Gallic acid, (+)-catechin, astragalin, astragalin-6"-O-gallate and isoquercitrin were isolated from Q. variabilis leaves. Gallic acid was isolated from all the leaves and could be a taxonomic index on Quercus spp..

Anti-oxidative Activities of Phenolic Compounds from barks of Pinus densiflora Siebold et Zuccarini

  • Kwon, Joo-Hee;Kwon, Yong-Min;Choi, Sun-Eun;Park, Kwan-Hee;Lee, Min-Won
    • Natural Product Sciences
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    • v.16 no.1
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    • pp.10-14
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    • 2010
  • Phytochemical examination of the barks of Pinus densiflora Siebold et Zuccarini has led to the isolation of one phenylpropanoid, one lignan, one flavonoid, one flavan 3-ol and two procyanidins : 4-O-$\beta$-D-glucopyranosyl-p-coumaric acid (1), 2,3-dihydro-2-(4-methoxy)-7-hydroxy-3-hydroxymethyl-5-(3-hydroxy propyl)-benzofuran 3-O-$\alpha$-D-glucopyranoside (2), taxifolin 3'-O-$\beta$-D-glucopyranoside (3), (+)-catechin (4), procyanidin B1 (5) and epicatechin-($4{\beta}$-8)-catechin-($4{\alpha}$-8)-catechin (6). Among them, Compound 4, 5 and 6 showed potent anti-oxidative activities and these anti-oxidative activities were significantly different compared with ascorbic acid as positive control.

A Study on the Extractives of Domestic Major Softwood Needles(I) - Antioxidant Activity of the Extractives from the Needles of Abies koreana Maximowicz and Abies holophylla Wilson - (국내산 주요 침엽수 잎의 추출성분(I) - 구상나무(Abies koreana Maximowicz)와 전나무(Abies holophylla Wilson) 잎 추출성분의 항산화 활성 -)

  • Lee, Sang-Keug;Choi, Don-Ha;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.34 no.3
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    • pp.73-83
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    • 2006
  • The dried needles (1.5 kg) of Abies koreana and Abies holophylla were ground, extracted with acetone-$H_2O$ (7:3, v/v), concentrated, and fractionated with a series of hexane, methylene chloride, ethyl acetate and water on a separatory funnel. Each fraction was freeze dried, then a portion of ethyl acetate soluble powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents. The isolated compounds were identified by cellulose TLC, $^1H$, $^{13}C-NMR$, COSY, HETCOR, FAB and EI-MS. The needles of Abies koreana and Abies holophylla contained a large amount of aromadendrin-7-O-${\beta}$-D-glucopyranoside (compound III), polydatin (compound VI), (-)-rhododendrol-2-O-${\beta}$-D-glucopyranoside (compound VII), in addition to a small amount of (+)-catechin (compound I), kaempferol-3-O-${\beta}$-D-glucopyranoside (compound IV), myricetin-3-O-${\beta}$-D-glucopyranoside (compound V), naringenin-7-O-${\beta}$-D-glucopyranoside (compound II). DPPH analysis was also tested to investigate the antioxidative effects on the isolated compounds and (+)-catechin and polydatin were effective.

Phenolic Compounds from Barks of Ulmus macrocarpa and Their Antioxidative Activities.

  • Kwon, Young-Min;Yeom, Seung-Hwan;Kim, Min-Ki;Lee, Jae-Hee;Lee, Min-Won
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.376.1-376.1
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    • 2002
  • Phytochemical examination of Barks of Ulmus macrocarpa isolated two flavanone, three flavanonol, three flavan 3-ol and one procyanidin compounds. We also determinated the antioxidative activity of these compounds by measuring the radical scavenging effect on 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Three flavan 3-ol (catechin, epicatechin and catechin-7-O-$\beta$-O-xylopyranoside) and procyanidin B1 showed significant antioxidative activity. (omitted)

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